A Girl From the Upper East Side
by BICaRdiBrEeZa
Summary: Includes anything that happened up until 2.08 Pret-a-poor-Jenny but from then on it's my idea of what i want for the future of these two kickass characters! Dan and Blair at Yale! Blair at the Humphrey for Christmas! Squeee!


Characters: Blair, Dan (Rufus, Nate and Jenny w/small mentions of Serena)

Ships: Blair/Dan FTW!!

Word count: 4000 ish

Summary: Includes anything that happened up until 2.08 (Pret-a-poor-Jenny) but from then on it's my idea of what i want for the future of these two kickass characters! Dan and Blair at Yale! Blair at the Humphrey for Christmas! Squeee!

I just included all three chapters because i ended up finishing it a lot faster than i thought i would ;-)

**Chapter One**

**One of Us Must Know**

The first time Dan Humphrey spots Blair Waldorf's red headband bobbing and weaving its way into a first row seat of the Yale lecture theater he swears his heart skips a beat, probably out of pure fear.

A cold sweat runs down his body and his hands twitch out in front of him in a knee-jerk reaction that sends his pen flying at the girl's head in front of him.

For the first time in two years he feels like the socially awkward loner Blair and her minions had labeled him as. And just great, he huffs to himself, he's right back in high school.

The redhead in front of him turns around with a scowl across her pretty face which quickly disappears when her eyes roam over Dan's face appreciatively, "I think you drop this?" She smiles flirtatiously wiggling his pen back and forth in front of him.

Dan's not paying attention though, his eyes are glued to the brunette in the front of the room, the ninety-five pounds of doe eyed evil he never thought he'd see again.

"Hello?" The redhead is annoyed with him, probably not used to being ignored, Dan smiles at her quickly before snatching his pen back and resuming his Waldorf watching.

He tried to recall the last thing he heard about her, "Blair didn't get into Yale, imagine the bitch fit she's going to have when she finds out you _and_ Serena did!"... He remembers Nate telling him that at the start of summer after school finished.

He didn't want to sound like an asshole at the time but he didn't get it. Yeah Serena was gorgeous, sexy and reasonably smart… but she had _nothing_ on Blair. Blair was easily the most intelligent girl to graduate from Constance-Billiard that year.

So Serena getting into Yale and Blair not getting in? It just didn't make sense to him.

Even at the time he felt some weird pang of sympathy for Blair, because he knew what it was like to not have your dreams come true. After all he and Serena never got their happily ever after.

He vaguely recalls Serena mentioning Blair was going to the University of Pairs in France, her dad lived there with his model boyfriend or girlfriend or something and Blair had explained to Serena emphatically that "La Sorbonne" as she called it was much more _cultured_ than _Yale_ and she would have gone there anyway even if she had been accepted to Yale.

The rest of details were fuzzy.

It had been a long time since he'd talked to Serena, over a year and a half, and the most vivid conversations they had that he remembered ended in tears or tantrums. It was hard to recall the small mentions of Blair he'd heard in between. He knew the two had lost contact though, he noticed it when Serena stopped saying "Blair this" and "Blair that".

Living half way across the country can do that to a friendship… or a relationship.

Serena got accepted to three Ivy League schools… _three_.

Brown, Yale and Princeton, but didn't end up going to any of them. She chose the Berkley and at first she didn't even tell Dan she'd been accepted there... after breaking up when she finally confessed she wanted to leave but didn't have the guts to tell him to his face, and then a following three months of trying to make it work living a thousand miles away, they both agreed to called it quits.

Almost two years later and Serena was dating some tree hugger named Chester while Dan was still exploring his options.

Its funny how drastically life can change, never in a million years would Dan have imagined not being with Serena van der Woodsen and the world not falling apart, then again he never would have imagined he's been sitting in a third year Yale lit class staring at the back of Blair Waldorf's head like some kind of scientist studying a newly discovered species.

"Dude!"

Dan's roommate, Jake, exclaims looking over at Blair, "She's smokin'!"

Dan's face transforms, the most horrific expression he can muster appears and Jake busts out laughing at his response.

"Am I interrupting your conversation gentlemen? Is there something more important to discuss than what's on your mid semester final?" Their professor barks at them, not in the mood for any bullshit.

"No! Sorry sir!" Dan squeaks and he doesn't have to look in her direction to know she's looking at him.

He could feel a Waldorf death stare from a mile away.

"Good." The professor replies pleased that Dan has enough humility to at least appear sincere, "As I was saying…"'

Dan doesn't hear one more word, his eyes are trained on his page, to chicken to see if he looks up whether she'll catch his eye or simply look away.

----+-----+-------

Barely a week later he spots her again, this time he's a little more prepared, after seeing her last week on his weekend visit home he immediately hit up Jenny for all the information he could about why Blair was back and how the hell she ended up at Yale.

"Nate told me she transferred on a spur of the moment, apparently she had awesome grades in France and all these great recommendations from different French newspapers she worked at while she was there or whatever so she re-applied to Yale for her final year thinking she's never get in and.. got in… go figure I guess she gets to go to her dream school after all. Order is finally restored in the universe." Jenny rolled her eyes signaling she clearly didn't believe the girl who made her high school life hell deserved such a reward.

Dan pretended to be just mildly interested, nodding and laughing at the appropriate times, but inside he was soaking up as much information as he could possible hold, his mind racing on overdrive.

He watches from his seat by the grass as Blair looks around the quad and then quickly scurries across it to the book store.

'Surprisingly, no girl mafia in tow', he thinks to himself. He knew Hazel went to Yale because he'd unfortunately encounter that _awful_ girl a few times since freshman year and he wondered why Blair was walking around all alone, it was so _unBlair_.

He doesn't even know how it happens but his suddenly ditching his coffee in the bin outside the shop and making his way inside.

Blair's talking to the cashier, who looks utterly petrified, she's waving her delicate hands around and the look on her face is anything but angelic.

"But I ordered the book three months ago! How could you possibly be out of ALL the text copies of 'Antiquity 303' already?!Why did you give away my copy?"

"maybe you should have tried ealier?" The boy stammers and Dan cringes knowing he's made a fatal mistake.

Blair's eyes narrow and she squares her tiny shoulders preparing for battle, "I was in another frakkin country you idiot! How was I supposed to get it any earlier?! Just teleport myself across the ocean?!"

The boy flinches away from Blair's tiny raging figure and checks the computer once more, "Sorry," he shrugs and offers a scared smile, "There's none left."

"Oh. My. God."

Blair huffs dramatically and turns around, Dan has to duck behind a shelf so she doesn't she him or storm straight through him, she's muttering something at rapid speed and Dan catches the word 'incompetent'.

He officially think he's lost his mind when his feet follow her down the footpath and his voice takes on a life of its own calling out her name, "Blair! Blair!"

She doesn't stop at first, and her tiny feet are moving much too fast for him to keep up, "WALDORF!"

It comes out wayyyy to loud and everyone within a five block radius spins around to look at him but it finally catches _her_ attention at least.

"Humphrey?" She questions, and when she turns around her face is contorted in confusion, clearly wondering what this raving lunatic is doing screaming her name in public.

He jogs the small distance to her and when he reaches her he sends a nervous glance around to make sure everyone has stopped staring.

There's a long awkward pause and Dan wishes the ground would open up and swallow him whole.

"Hi," he says and it sounds so much more pathetic out loud than it did inside his head.

"Hi," she smiles bemused by the whole interaction, all traces of hostility gone.

"I have what you're looking for back in my dorm room," Dan blurts out in a rush eager to fill the void of awkwardness.

Blair gaps at him and it takes a second for the double meaning of his words sink in, "No no no I mean I have that _book_, I did that subject last year!" He clarifies quickly, "That sounded kind of like a pick up line, didn't it?" He laughs nervously and he's never felt like more of a spaz in his entire life.

Blair laughs too and he realizes now that it's not the same laugh he's used to hearing, it's... _friendlier _somehow. It's bubblier and has a much sweeter tone, no trace of malice evident. It's like she's laughing _with_ him as opposed to _at_ him.

"If I didn't know better I would think you were trying to get me in bed Humphrey." Blair wiggles her eyebrows up and down suggestively and it's quite possible the most adorable thing Dan's ever seen.

They both laugh at the absurdity of such a situation and the ice is finally broken.

**Chapter Two**

**Don't Think Twice, It's Alright**

Dan remembers now the last real conversation he had with Blair and when he does, he wonders how he could have ever forgotten it.

"I wanted to tell you, I heard about you and Serena, I'm really sorry." Blair voice is soft and Dan takes the time to look up from his notebook and study her face.

She looks so different but still so familiar. She's older, more mature, and she wears her hair parted slightly to the side with long dark locks hang down her shoulders.

Her face is still as pale as porcelain and her cheeks rosy pink.

She always reminded him of snow white.

Her eyes are what capture him though; the sincerity behind the brown orbs is unquestionable.

Dan shrugs, "That's life, you know?"

"Yeah," Blair nods; she knows exactly what he means.

He bitterly reminds himself he's one of the reasons her life didn't work out the way she planned it.

Senior year Serena had thought it would be a brilliant idea for Dan to advise Blair on her love life, it turned out to be a total disaster. And the last thing Dan ever said to Blair caused her to lose someone she loved, maybe the last guy she really loved.

She didn't say one word to him for the rest of the high school year.

"You're holding my heart together with your words," Blair sings the words softly and Dan raises an eyebrow at her, "It's from a French song… you reminded me of it just then."

He feels like shit when he notices she's tearing up.

She was probably thinking about the same smug asshole he was, Chuck Bass.

"Hey, you want to get out of here? I'm going home for Christmas... Come with me?" Dan says it and doesn't even think about what it means.

They've only been hanging out for a few months (nine months and three days to be exact not that he's counted or anything) and he'd just barely consider them friends they were more like acquaintances who hung out all the time and talked a lot and sat with each other during lunch but definitely definitely not friends, so maybe she would find this invitation totally out of the blue.

He frowned because he was having a hard time even convincing himself there wasn't something extraordinary between them.

Jenny, Rufus, Nate's faces filter through his mind, all the people who'll want to know why the hell he'd bring Blair Waldorf to their door. He hadn't told anyone about their studying sessions or coffee catch ups or late night phone calls. He wonders why no one questions him about it and then understands she probably hasn't told anyone either or maybe she just got no one to tell.

"Well alright," Blair says with a pretty smile and it's contagious.

He finds himself goofily grinning back with his own lop-sided smile.

Alright.

-----+------+-----

He can feel the tenseness of her stiffened back pressing against him.

Part of him really wanted to show her life on his side of the block wasn't as bad as she thought and another part of him couldn't resist the hilarity of seeing Blair Waldorf on the subway.

Trying so hard not to laugh at her every disgusted and appalled reaction, he nudged her forward with his chest to indicate this was their stop.

To her credit she hadn't complained once, he was starting to think something was wrong with her.

"You doing okay there?" He asked when they were sitting in their taxi cab just a few blocks from the loft.

She shot daggers at him and he finally lost it.

Laughing uncontrollably he couldn't even catch his breath.

"Oh don't think you're getting off without a punishment Humphrey," Blair poked her finger into his chest, "Blair Eleanor Waldorf doesn't get on the subway for just anyone."

He stops laughing and they both stared at one another with serious faces, Blair cracks a smile like she can't keep up the charade and looks out the window.

He wasn't just _anyone_ anymore and both of them knew it.

-----+------

"Welcome to our humble abode!" Rufus threw the doors open with dorky hand flourish.

"She's been here before Dad," Dan deadpanned pushing past his father and dragging Blair along behind.

He'd told his father about Blair coming right after he'd asked her, so at least one Humphrey know knew about the developing friendship. Dan let Rufus break the news to Jenny but apparently she didn't take it too badly, probably too baffled to even form a response.

"Hello again Mr. Humphrey," Blair said sweetly extending her hand for him to shake and Dan tried not to roll his eyes at her. Blair had a habit of putting on a perfect princess persona around anyone she was trying to impress.

Grabbing onto Blair's small hand, he made a beeline for his room, Blair was stumbling behind in her heels, "Where's the fire?" Rufus called after them but Dan had already slammed the door shut.

He needed to get away from his father before he said something that put Dan in the shit. Dan had maybe kind of forgot to tell Blair that Nate was going to be visiting from Dartmouth this weekend, not sure if the reaction from Blair would be pleasantly surprised or nuclear meltdown worthy, he held out the information for as long as possible.

He wasn't really sure how things between the ex-high school sweethearts were, Nate and Blair never talked about each other, and Jenny's opinion of Blair wasn't exactly favorable so he wondered whether as a loyal boyfriend Nate was obligated to feel the same way.

"Okay I need to tell you that Nathaniel Archibald is coming this weekend and staying here with us in this loft and I'm sorry I didn't tell you earlier but I thought if I told you that _and_ then told you we were taking the subway you wouldn't have come," Dan voice had surely just broken record rambling speed.

"Okay."

Blair looked at him as if he'd grown a second head.

"Do you still want to stay? I'll understand if you don't…" Dan mumbled nervously and it only just occurred to him how much he had been looking forward to bringing her here.

"Are you kidding? Like I would ditch you after how much you've been talking about these holidays," Blair rolled her eyes, "I'd never hear the end of it."

Dan laughed, "Fair point."

"So you'll be okay?"

"Dan," Blair said picking up Cedric and giving him a kiss on the forehead, "You talking to Blair… I'm going to be fine."

"So it's not too awkward?" Dan prodded.

"No," Blair shrugged fingering through his book collection, "Nate and I talk sometimes. He called me a little while back to ask for some help getting Jenny a birthday present."

"Oh," Dan wasn't expecting that.

He suddenly felt the need to have every single detail about the encounter.

"I mean it's not like where BFF's," Blair continued noticing the frown on Dan's face, "We don't like each other, we just don't hate each other, we don't _anything_ each other."

"Hmm" Dan hummed distractedly.

Blair brought her hand in front of her chest defensively, "What? Are you angry at me now?"

"No, no. I just… you never mentioned you talked to him." Dan replied and it was absolutely impossible to miss the jealously in his voice.

Instead of getting annoyed at him like she might have in the past Blair smiled like she knew a secret he didn't.

"What?" He bit a little annoyed that he was feeling jealous and even more annoyed that he couldn't hide it.

"You're cute when you're jealous."

Blair leans forward and kisses him on the lips.

Dan's heart skips a beat and now he knows it's not out of fear like he first thought that day he spotted her in the lecture theater.

He's falling for her, no he isn't falling because that implies some sort of transiting period. He's already fallen completely in love with this girl from the Upper East Side.

**Chapter three**

**Don't Fall Apart on Me Tonight**

Jenny and Blair were surprising civil towards each other. Actually they were kind of acting… nice.

Dan was wondering if maybe he had accidentally stumbled into an alternate universe as he watched the two giggling and gossiping on the sofa.

"Girls," Nate said, as if it explained everything Dan had just been thinking about, he came to help Dan with the dishes.

"Yeah," Dan nodded and smiled at the taller boy handing him a cup to dry.

"I finished that rough copy of your novel you sent to me last month. I love the title, '_A Girl on the Upper East Side'."_

Dan almost drops the plate he's holding.

"Oh-oh, you did?" He stutters suddenly wishing he hadn't of brought Blair for the weekend.

His eyes find hers she's listening to Jenny and Rufus talk about a summer trip the family took to California, she can't hear him but she pokes her tongue out at him from her seat in the lounge room.

Dan never really saw his friendship with Blair as a long term thing, he sort of figured it would fizzle out once they stopped having classes together next semester, but now, he couldn't imagine not having her in his life as such a permanent fixture.

"It's really good. I like how you sort of took everything about Serena and reversed it. I don't think she'll realize it's about her… if you were worried about that? It was really smart not psychically describe the character, it let's the reader imagine what she's meant to look like," Nate says grabbing the plate from Dan's frozen hands.

"Serena?" Dan asked completely confused.

"Yeah Holly, the love interest?" Nate says as if it's Dan that doesn't understand, "She's like the anti-Serena right?"

"Oh, right right." Dan nods and chuckles.

After a few minutes of silently washing the dishes Nate turns to face him.

"And man it was really good of you to invite Blair over; I know she's not the easiest person to get along with. And I'm surprised you even got a hold of her actually," Nate said furrowing his brow.

Dan felt uncomfortable with the turn in the conversation, "I haven't talked to her in a while… she's always too busy at Yale. How did you convince her to come? Offer to take a final for her?" Nate laughed and Dan faked his own.

Sometimes it was good having a friend so socially retarded like Nate. He hadn't the slightest clue that Blair was so much more to Dan than just someone he felt sorry for.

Now that he thought of it Dan was actually nervous about sending his short novel to be published… he wondered if anyone else would put two and two together.

Holly Hepburn and Holden Humphrey... it wasn't such a stretch to think of Blair and Dan. In fact it was kind of blatantly obvious and that's why he chose it, it was kind of like an inside joke to himself and to Blair if she ever read it.

When he wrote it he never thought anyone would know it was about him and Blair, firstly because he never thought she'd ever give him the time of day in the first place let alone spend most of her spare time with him and secondly it was just too hard for anyone who knew them to imagine someone like Dan falling in love with someone like Blair and vice versa.

But it happens, he reminds himself, and is surprised that the first couple that comes to mind is Rufus and Lily.

Opposites really do attract.

-----+----+---

Dan tries to be discreet as possible, placing the blanket ever to carefully over Blair's arm just enough to hide the fact he's holding her hand it underneath it. He looks up and catches a smile on her face, Blair squeezes his hand tightly. She looks over quickly at Nate and Jenny and relief is written across her face when she sees them too consumed in the movie to notice what is going on around them.

Both Dan and Blair jump a little when Rufus comes out from kitchen area, "Nate don't forget to make up the couch when you go to bed," He says implying he better not catch the twenty one year old sleeping in his eighteen year old daughters room again.

"He will dad!" Jenny scoffs but the pinkness of her cheeks gives her embarrassment away.

"What about Blair?" Jenny mocks before Rufus can walk away.

"Uhhh," He stumbles clearly not having thought of that sleeping arrangement, "Ummm" he looks towards Dan as if silently asking him what the answer is.

"She's in my room." Dan replies confident enough not to have to ask her, he turns his attention towards the television but not before hearing Jenny huff, "Totally unfair."

Blair squeezes his hand once more and lays her head on his shoulder, using him as a pillow.

Feeling a pair of eyes on him Dan looks around and gulps, Nate is looking in between Dan and Blair analyzing the pair, he wonders if things have finally clicked in Nate's brain.

Blair interrupts the panic in his brain with a yawn, "I'm sleepy, bed time."

She sounds like a purring kitten when announces it and as she stretches her body out like a cat Dan's attention is drawn to the creamy skin of her back now exposed by the rising of her shirt.

"Night," Blair mumbles and pats Jenny on the head affectionately.

Dan is slow to rise and Blair makes her way to the room before he's even standing.

"Dan," Jenny whispers only loud enough for her Nate and him to hear, "I was skeptical at first but after witnessing it myself.. I approve."

"You approve of what?" Dan asks confused watching Blair walk into his room.

Jenny motions between his place in the lounge and his bedroom Blair just disappeared into behind them.

"You two, the whole Blair and Dan dating in secret thing, you don't have to hide it anymore," She rolls her eyes, "Besides you're kind of bad at it," and laughs.

He genuinely smiles at his little sister and is grateful she's matured so much over the last year in part due to the boy sitting beside her, "Thanks Jen. It's not exactly like we meant to be together in secret," Dan says sending a nervous glance in Nate's direction, "but thanks for not freaking out."

"You're welcome," she says and pushes him with her foot towards his bedroom, "Night loser!"

----+----+----

"So I'm not really sure how this works…" Dan says as he walks into his room he quickly trails off when he sees what Blair is wearing to bed.

She looks up when he speaks and is confused when he stops, her hair is messy and loose, dark tendrils fan out across his grey pillows. She's lying on her back one perfectly smooth leg under the covers and the other tantalizingly outside.

Her Yale tank top somehow matches his blue plaid boxers as if they were made to be worn together, "I hope you don't mind," she looks down at his boxers that run a border across her lower stomach, "It's too hot in this loft to wear my pajama pants."

"Uhhh," He gulps and the sound is heard by both of them.

Blair's lips are curved in a sly smile and he suddenly realizes she's actually doing this on purpose.

He looks away and can't help but blush, "Blair Waldorf you are pure evil."

She giggles loudly and he's embarrassed to think what everyone else in the apartment must be thinking.

"You love it!"

He smiles broadly and finds himself doing something completely crazy, your insane Humphrey she's driven you insane.

"No, I love you."

Before he has the chance to being rambling or chicken out, Blair reaches up and pulls him into the bed with her, jeans, shoes and all.

He's still holding her heart together with his words, but she's not broken anymore, if she wanted too she could let him go and be fine.

"I love you too," Blair whispers into his ear.

But she doesn't and she won't.

He kisses her slowly and softly then quickly with a burning desire to be as close to her as possible the pace of their passion taking over.

And it feels right, everything feels just right tonight.

---+---+----

**TWO YEARS LATER**

Dan sat with his laptop resting on his lap, laughing at Blair scoring a touchdown against his dad. They were playing the girls vs. boys game of football, a Humphrey Christmas tradition, and he voted to be umpire because he still had a few pages to edit for his novel and wanted to get it done before his publisher called him to complain...

He continued typing determined to finish the last page.

"_And he couldn't believe it; he'd gone and done something completely insane._

_He'd fallen in love with a perfect girl from the Upper East Side who probably couldn't even tell you his name."_

He pressed backspace on what he'd written after his first sighting of Blair Waldorf at Yale three years earlier because now he knew how his first official novel _should_ end.

"_And he couldn't believe it; he'd gone and done something completely insane._

_He'd fallen in love with a perfect brunette girl with porcelien skin and brown doe eyes from the Upper East Side,  
_

_A girl whom he hoped would be the one girl to take his last name."_


End file.
